Oakland Vacations from $369
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport
Price was $471, price is now $369 per person
$369
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
Our room was clean. It looks like they need some renovation.
Reviewed on Jun 15, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $696, price is now $488 per person
$488
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,534 reviews)
Great location to everything
Reviewed on Jun 14, 2026
Stay Pittsburgh
Downtown Pittsburgh
Price was $1,060, price is now $795 per person
$795
per person
Sep 3 - Sep 6
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Pittsburgh (PIT)
8/10 Very Good! (290 reviews)
Third time staying at the property. Minor issue with the elevator being out of service for a couple of days, but otherwise another pleasant stay. Will definitely be back when I’m in the area.
Reviewed on Jun 14, 2026
Crowne Plaza Suites Pittsburgh South by IHG
Price was $677, price is now $513 per person
$513
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Exceptional service from everyone. The breakfast staff were awesome! Completely accommodating and helpful staff all around.
Reviewed on Jun 13, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was $678, price is now $523 per person
$523
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,072 reviews)
Valet parking was an easy process.
Reviewed on Jun 12, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
$119 nightly
The price is $136 total per night from Jun 28 to Jun 29
$136 total
Jun 28 - Jun 29
Total with taxes and fees
9/10 Wonderful! (752 reviews)
"Ray at the check in desk was amazing 👏 Our only complaint was that the parking lot was full when we got back and had to park in the garage."
Reviewed on Jun 14, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Jun 21 to Jun 22
$145 total
Jun 21 - Jun 22
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"Perfect in every way!!!"
Reviewed on Jun 14, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $222 total per night from Jun 21 to Jun 22
$222 total
Jun 21 - Jun 22
Total with taxes and fees
9.2/10 Wonderful! (784 reviews)
"This was such an AMAZING hotel! Beautifully decorated! Loved the gym and the top floor restaurant and bar. The staff was SUPER nice"
Reviewed on Jun 15, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Explore a world of travel with Expedia
- Pittsburgh Hotels
- Hotels near Downtown Pittsburgh
- Hotels near University of Pittsburgh
- Hotels near University of Pittsburgh Medical Center
- Hotels near Petersen Events Center
- Hotels near Soldiers and Sailors Memorial Hall and Museum
- Hotels near Cathedral of Learning
- Hotels near Heinz Memorial Chapel
- Hotels near Carnegie Library of Pittsburgh
- Hotels near North Oakland
- Hotels near Carnegie Museum of Natural History
- Hotels near Pittsburgh Playhouse
- Hotels near Central Oakland
- Hotels near Tour-Ed Mine
- Hotels near Carnegie Museum of Art
- Cheap Hotels in Pittsburgh
- Hotels near PNC Park
- Hotels near Phipps Conservatory
- Hotels near PPG Paints Arena
- Hotels near Carnegie Mellon University
- Hotels near South Oakland
- Hotels near Schenley Park
- Hotels near Acrisure Stadium
- Hotels near UPMC Shadyside
- Hotels with Free Airport Shuttle in Pittsburgh
- Hotels near Shadyside
- Hotels near Strip District
- Hotels near Pittsburgh Opera
- Hotels near Gallery G Glass
- Extended Stay America Hotels in Shadyside
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- Marriott Hotels & Resorts in Shadyside
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- Hotel Wedding Venues Hotels in Shadyside
- Resorts & Hotels with Spas in Shadyside
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- Casino Hotels in Shadyside
- Hotels near Bloomfield
- 4 Star Hotels in Bloomfield
- Extended Stay Hotels in Bloomfield
- Pet-Friendly Hotels in Bloomfield
- Casino Hotels in Bloomfield
- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- Ppg Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
- Car rentals near Pittsburgh
- Car rentals near University of Pittsburgh Medical Center
- Luxury Car Rentals near University of Pittsburgh Medical Center
- Car rentals near University of Pittsburgh
- Car rentals near Heinz Memorial Chapel
- Car rentals near Phipps Conservatory
- Car rentals near Carnegie Mellon University
- Premium Car Rentals near Carnegie Mellon University
- Car rentals near UPMC Shadyside
- Car rentals near Shadyside
- Hertz Rental Cars in Shadyside
- Enterprise Rental Cars in Shadyside
- Surprice Car Rentals Rental Cars in Shadyside
- Car rentals near Bloomfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.